How to ask someone to be your business mentor

Two people meeting together The Beermat Entrepreneur reckons every startup entrepreneur should have a mentor. So do many TV programs about business, from Dragon’s Den to the Apprentice. The Prince’s Trust, a British charity that helps young people start businesses, will only fund a business that works with one of their mentors.

I ran my own computer games company for more than a decade. Since I sold it in 2000, I have been approached by eight or nine people to be their mentor. I helped one company for three years. I was also a mentor to two Prince’s Trust businesses. This post is based on the experience of being asked, rather than the experience of asking.


  1. Remember that you are asking a favour. Generally people want two to four days a month of my time. Unpaid. This time isn’t free to me. Usually it means giving up my free time to do it. One or two people seem to expert 24/7 phone and email support plus an instant, passionate commitment to their company. Uh oh!
  2. Have a business plan. Even if it is one or two sides of paper. I need to know that you have spent more than five minutes thinking about your business. I’m not a VC – it doesn’t have to be perfect or complete. I can help with that. It’s not a mentor’s job to come up with a business plan for you.
  3. Have a plausible business. It’s good if you can show some kind of product, website, demand or sales. At the very least, be serious about starting your business. Several people have come to me while still in full-time employment and virtually asked me to start their business for them before they would quit. This isn’t a mentor’s role.
  4. Show me a reason to do it. It doesn’t have to be money. In fact, I never received a penny from the three businesses I did mentor. But the product has to be interesting, the journey promising, perhaps there’s a possibility of equity or fees down the line. In one case, I mentored a personal training company and we time swapped: training for mentoring. If I’d charged them a full commercial rate for my time, it would have been unfair but swapping one hour of my time for one hour of their time seemed fair without being expensive.
  5. Make contact by introduction or recommendation, if possible. An email out of the blue is less likely to get a hearing than an introduction from a mutual friend.
  6. Do your homework on your would-be mentor. It’s more like a seduction than a recruitment exercise. Find out what your person is interested in, what is likely to motivate them, who they know and what they might be able to contribute. Use that information when you’re making your approach.
  7. Do ask someone who has something to offer. Uncle Tom may be a good chap, but you need a mentor who has been through the process of starting a business themselves.


  1. Don’t be late for meetings. More than any other business relationship, the mentor relationship depends on trust and respect. Being flaky, especially when you are courting a mentor, is a recipe for disaster.
  2. Don’t expect your mentor to run your business. A mentor isn’t a manager or a director. If you want a manager, hire one. If you need a lawyer or an accountant, hire them.
  3. Don’t take them too seriously. It’s your business, not their’s. You have to make the decisions and even I have been known to make the occasional mistake.
  4. Don’t ignore their advice. I quit mentoring one firm because they simply would not listen to the key point I was making: the reason that they were not growing or making a profit was because they did no marketing at all. No customers, no revenues. The entrepreneur was happy building a better mousetrap but figured that people would come to him by telepathy. The main reason to have a mentor is to see a bigger picture. Ignore it at your peril.
  5. Don’t confuse investors with mentors. I have spoken to several successful businessmen who have taken on angel investment because they really liked the person with the money and thought they would be good mentors. In two cases, the relationship soured quickly and the investor became a thorn in the flesh and, in both cases, ended up driving the original entrepreneur out of the business.
  6. Always ask before using their name. Another mentoree added my name to all his websites and correspondence, naming me as a non-executive director of the company (I wasn’t). Not good.
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11 Responses to How to ask someone to be your business mentor

  1. Doug says:

    The is a very good primer. I asked the leader of a VC angel group that decided NOT to fund my company to be my mentor. My goal was not to convince him that we WERE good enough to get the cash rather getting me where I want to go with the company and overall career.

    I created an in depth biography, gave goals, asked questions, etc. We have a very good relationship and I’m concious of not overstepping that boundary into “please tell me what to do with my company”. He’s introduced me to many high level contacts and positioned me as “an expert” to be listened to for some.

    Although not critical, I think we can all use this kind of coaching. I try to model his behavior…and if I do it properly, perhaps someday I’ll be a VC and mentor as well.

  2. Hi Matthew

    Loved this list – it’s just what my target audience of aspiring physician entrepreneurs needs to help them step away from the independence they are accustomed to, and reach out for help.

    In today’s post, I quoted your list of “do’s and don’ts” on my new blog, as you said it better than I could!

  3. David says:

    Thanks for those great pieces of advice. It’s easy to say that they’re common sense, but unfortunately so many people don’t practice common sense!

  4. Finally, someone who knows what it feels like being a mentor! Your first point said it all: some people will take a mile if you give an inch. I am quite generous myself, but I’ve been hiding this quality because some people just don’t have a clue. I would add another point: watch out for the bias. Common wisdom has it that nothing is given so freely as advice: many people will simply advise you to be like them. I like mentors who will guide me, but will still allow me to be myself.

  5. Business mentors are for your help and not for running your business. Always remember business mentors are for developing your business growth.

  6. Good work Matthew.

    I’ve been advising business owners for 13 years and the horror stories I hear about would-be mentors are rarely good.

    I wish every business owner had your list handy before engaging one, the reputation for mentors would be much higher.

    • Hi Tim, thanks for the comment. There are a lot of terrible business advisors out there and I would counsel any business owner to be especially careful before they *hire* someone as a business mentor. But the kind of mentoring I’m talking about is free; typically under the auspices of a scheme like the Prince’s Trust. Still, even then, I think business owners need to take advice with a pinch of salt. A lot of so-called advisors are like eunuchs in a harem. They see it done all day but they’re not up to it themselves.


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